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Welcome to this EASTER SPECIAL – Episode 284 of the MSP Marketing Podcast with me, Paul Green.

How one big decision changed this MSP owner’s life

Featured guest: Steve Dempsey has been a Managed IT Services owner for over 25 years and only serves small businesses in several different markets in the UJS. In addition he owns a small SEO agency for MSP’s only to help them generate local organic leads for their business.

Hello and welcome to this special for Easter. I’m joined today by MSP owner Steve Dempsey, who’s going to tell us his business owning journey. And trust me, you have never heard a story like this before. There are many highlights, one of the best being how he went from losing thousands in his business every month to making thousands, with one key decision. Steve is a unique and generous character, and you are going to love everything he has to talk about.

Hey there, I’m Steve Dempsey. I’ve been in the IT business for 25 years and my main IT company is NeoTech Networks.

And it’s so cool to finally get you here onto the podcast, Steve. We’ve got our special episode for Easter 2025, and I feel like you and I have both been in lots of the same places at the same time, but we’ve never had a quality conversation. You’re obviously highly active in The Tech Tribe, as am I. We nearly met at Scale Con, which was the big marketing conference in Vegas in October last year. I actually talked to you from the stage and we did some cool stuff where you were in the audience and I was on the stage, but we never found each other afterwards, so it’s absolutely crazy. But I’m delighted to have you here on the show. And the reason I want to have you here, well there’s two things that I want to talk about. The first of them is you are one of the most unique MSPs that I have ever come across and you have a very unique lifestyle and I want to explore today what your life is like and what you’ve had to go through to get to that life.

And just as a bit of a tease for the many MSPs that will be listening to this on the podcast or indeed watching this on YouTube, Steve has an enviable lifestyle and it’s nothing to do with having lots of houses, a yacht, cars, anything like that. But Steve is living his best life and also has a great business. So that’s what we’re going to explore first of all. And then secondly, you have one of the most unique approaches to SEO, search engine optimisation, that I’ve ever come across. So I want to explore that because I know you had a huge amount of success for it, and indeed you are helping a small number of other MSPs to implement that in their business. But let’s start with the lifestyle stuff. So first of all, Steve, let’s hear your story. So you said in your intro you’ve been in the tech world for 25 years, which sounds like such a long time, doesn’t it? I’m 50. How old are you right now?

I’ll be almost 52.

Okay, so we’re more or less the same age then. Talking about 25 years, it sounds a lot and when you realise, hmm, that’s half of my life actually, that’s quite sobering in some respects. Tell us about your tech career then. So how did you get into tech in the first place? How did you start your first business? What’s your journey into this MSP space?

To sum it up quickly, full disclosure, I actually never went to college. I only have a high school diploma and I’ve always had an entrepreneurial spirit. My last full-time job was, this is probably embarrassing to admit it’s been that long, my last full-time job was probably 28 years ago. The company went out of business. I always had that just drive in me to do something on my own. And then when I was 27 years old when I was on my own, I started a quote on quote computer company. Let’s just say that I had absolutely no idea what I was doing and absolutely no direction whatsoever. But on the second year I actually did start to get the clients and I actually went to people’s homes and repaired computers and all that good stuff.

Yeah, the real old fashioned way of doing it. And when did you make the leap over into managed services?

You’re going to love my brutal honesty, Paul, on everything because I am a New Yorker and I think you know me well enough from The Tribe, I don’t hold back and I don’t mince words. Truth be told, a number of years later, 15 years about, I admit I was getting burned out and I did have, and I fully admit this, I had an attitude problem. I had an attitude problem for years. I think just over the work and just dealing with everything, I really let my business slide and it was pretty bad. And then when I turned 40, it’s that whole midlife crisis thing, I got burned by another IT owner in New York City that I was subcontracting for, and then that’s when I had the final aha moment of I need to make a decision. I either need to get serious about my business, or get out. And I’m 40 years old, I’m like, you need to grow up or get out. And it was at that moment that I went full swing into my IT business virtually overnight reinvented my perspective, I got rid of my attitude problem, I saw everything as brand new and I hired my first employee probably about a year later.

Amazing. When you talk about that attitude problem, what was that? Was that you being arrogant or was that just being a bit of an arms folded New York IT guy, everyone else is an idiot, that my way is the only way? Or was it something different?

Nope, actually the attitude problem was actually I just didn’t want to be bothered. And I did get fired by a couple of clients, and looking back on it I’m very embarrassed by it. I’m sure people picked up on it. I just didn’t want to be bothered, to lift a finger. I think part of it came from just the repetitive work. I mean when you fix someone’s Outlook or printer or whatever for the 500th time, you’re just like, yeah, I just don’t want to be bothered anymore. And it showed, I admit it.

Yeah, I think that’s very brave of you to admit that because I’m not a psychologist, but this feels like a therapy session for you, to go back and even to look at an aged fault of something that you are 10, 12 years on from. None of us like to admit our faults and when our behaviour didn’t match up to our values. So thank you for doing that. I think at least one person listening to this will realise that, oh my goodness, that’s me. I’m trapped in that because I’m dealing with the same things and I’m trapped in something I actively dislike. In fact, we have a phrase for it, which is where MSP owners create a prison of their own design and lock themselves inside, and I think it manifests itself in different ways, and that was clearly how that manifested for you.

So you got to that point, you had that incident, you made the decision to do it properly or get out of it. Obviously you went in a specific direction. What then happened to the business and take us through the story of how you grew that business. I assume you got more staff, you got more clients. Is it your traditional growth story?

It is traditional growth. I did get more. I elevated each year. I got a small office in Manhattan, for the first time in my life I actually had an office and then things grew from there. A couple years later I needed to hire a second tech and get a bigger office. And like I said, I was just on full swing looking back on what held me back at that time. I’m sure other solo IT guys would appreciate this, even for me to hire my first employee, it probably took me, and I’m not kidding, a year to mentally get over the fact that I was paying somebody a full-time salary for work that I could do myself. And the reason why is because I was not a business owner, I was a tech. I was 90% tech and I was not a business owner. So for years, even five years, I was more of a tech than a business owner. And then I finally started to slip over to the other side and realise I needed to get other people to do things for me and do the work, so that I can move on to bigger and better things.

That mindset shift from being a tech who happens to be working within their own business, to being the business owner who is working on almost a different level, you’re working on growing this thing and that means having to get people in to do things that even though you can do them. Is that a mindset shift that you could have done earlier or do you think you had to go through that process to get to that point?

I think it probably depends on the person. You really need to think big. And I kind of do think big now, but I just wasn’t mature enough or did not have the business sense to think big. But I honestly can say 100% what changed all that was The Tech Tribe, which we knew was going to come up sooner rather than later. Once I joined The Tech Tribe brand new and I started to absorb all that knowledge and then be around not only other business owners, but also other business owners that had 5, 10, 20 staff. Jamie Warner for example comes to mind, who’s a friend of mine now, hearing like wow, he actually has people that work for him and he’s not dealing with his low level stuff. And once that started to rub off on me, it took years, but yeah, that definitely started my transition of thinking like a business owner and not a tech.

I love that. And Jamie Warner has been on this podcast a couple of times. He’s such good value because as you say, he’s built an enormous MSP and he’s built Invarosoft as a side project and it’s huge. And Jamie’s just one of the most inspirational people you can speak to, which